The bicorannulenyl dianion: A charged overcrowded ethylene

David Eisenberg; Edward A. Jackson; Jennifer M. Quimby; Lawrence T. Scott; Roy Shenhar

doi:10.1002/anie.201002515

The bicorannulenyl dianion: A charged overcrowded ethylene

David Eisenberg, Edward A. Jackson, Jennifer M. Quimby, Lawrence T. Scott, Roy Shenhar^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

Super bowl: Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double-bond character of the connection between the two bowls. Three stable diastereomers that interconvert through bowl inversions and central bond rotations were shown to exist.

Original language	English
Pages (from-to)	7538-7542
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	41
DOIs	https://doi.org/10.1002/anie.201002515
State	Published - 4 Oct 2010

Keywords

Annulenes
Carbanions
Conformation analysis
Conjugation
Overcrowded ethylenes

Access to Document

10.1002/anie.201002515

Cite this

@article{7e5b38a99ab94230ab55bcdd53e600b0,

title = "The bicorannulenyl dianion: A charged overcrowded ethylene",

abstract = "Super bowl: Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double-bond character of the connection between the two bowls. Three stable diastereomers that interconvert through bowl inversions and central bond rotations were shown to exist.",

keywords = "Annulenes, Carbanions, Conformation analysis, Conjugation, Overcrowded ethylenes",

author = "David Eisenberg and Jackson, {Edward A.} and Quimby, {Jennifer M.} and Scott, {Lawrence T.} and Roy Shenhar",

year = "2010",

month = oct,

day = "4",

doi = "10.1002/anie.201002515",

language = "אנגלית",

volume = "49",

pages = "7538--7542",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "41",

}

TY - JOUR

T1 - The bicorannulenyl dianion

T2 - A charged overcrowded ethylene

AU - Eisenberg, David

AU - Jackson, Edward A.

AU - Quimby, Jennifer M.

AU - Scott, Lawrence T.

AU - Shenhar, Roy

PY - 2010/10/4

Y1 - 2010/10/4

N2 - Super bowl: Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double-bond character of the connection between the two bowls. Three stable diastereomers that interconvert through bowl inversions and central bond rotations were shown to exist.

AB - Super bowl: Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double-bond character of the connection between the two bowls. Three stable diastereomers that interconvert through bowl inversions and central bond rotations were shown to exist.

KW - Annulenes

KW - Carbanions

KW - Conformation analysis

KW - Conjugation

KW - Overcrowded ethylenes

UR - http://www.scopus.com/inward/record.url?scp=77957572244&partnerID=8YFLogxK

U2 - 10.1002/anie.201002515

DO - 10.1002/anie.201002515

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:77957572244

SN - 1433-7851

VL - 49

SP - 7538

EP - 7542

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 41

ER -

The bicorannulenyl dianion: A charged overcrowded ethylene

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this